{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

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Chemical Name:{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane
CAS No.:314021-43-7
Molecular Formula:C₃₅H₄₄O₅SSi
Molecular Weight:604.883
Hs Code.:

{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2<i>H</i>-pyran-2-yl]-pent-4-enyloxy}-<i>tert</i>-butyl-diphenyl-silane

Synonyms:{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

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Chemical Property of {5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

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Technology Process of {5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

There total 11 articles about {5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

: 314021-42-6
(4Z,8E)-(S)-1-Benzenesulfonyl-12-(tert-butyl-diphenyl-silanyloxy)-7-triethylsilanyloxy-dodeca-4,8-dien-3-one

: 67-56-1
methanol

: 314021-43-7
{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

Guidance literature:: (4Z,8E)-(S)-1-Benzenesulfonyl-12-(tert-butyl-diphenyl-silanyloxy)-7-triethylsilanyloxy-dodeca-4,8-dien-3-one; With triethylamine hydrofluoride; In methanol; dichloromethane; water; for 1h;

methanol; With pyridinium p-toluenesulfonate; In dichloromethane; water; for 0.5h; Further stages.;
DOI:10.1021/ol006674w

Reference yield:

: 314021-28-8
(E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-non-5-en-1-yn-4-ol

: 314021-43-7
{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; various solvent(s) / -78 - -10 °C

2.2: CeCl₃ / tetrahydrofuran; various solvent(s); pentane / 0.33 h / -78 °C

2.3: 63 percent / tetrahydrofuran; various solvent(s); pentane / -78 - -30 °C

3.1: 57 percent / H₂; quinoline / Lindlar's catalyst / various solvent(s)

4.1: Et₃N*HF / CH₂Cl₂; H₂O; methanol / 1 h

4.2: 64 percent / PPTS / CH₂Cl₂; H₂O / 0.5 h

With 2,6-dimethylpyridine; quinoline; n-butyllithium; hydrogen; triethylamine hydrofluoride; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Silylation / 2.1: Metallation / 2.2: Substitution / 2.3: Acylation / 3.1: Hydrogenation / 4.1: Desilylation / 4.2: Cyclization;
DOI:10.1021/ol006674w

Reference yield:

: 314021-29-9
C₃₁H₄₆O₂Si₂

: 314021-43-7
{5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / -78 - -10 °C

1.2: CeCl₃ / tetrahydrofuran; various solvent(s); pentane / 0.33 h / -78 °C

1.3: 63 percent / tetrahydrofuran; various solvent(s); pentane / -78 - -30 °C

2.1: 57 percent / H₂; quinoline / Lindlar's catalyst / various solvent(s)

3.1: Et₃N*HF / CH₂Cl₂; H₂O; methanol / 1 h

3.2: 64 percent / PPTS / CH₂Cl₂; H₂O / 0.5 h

With quinoline; n-butyllithium; hydrogen; triethylamine hydrofluoride; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Metallation / 1.2: Substitution / 1.3: Acylation / 2.1: Hydrogenation / 3.1: Desilylation / 3.2: Cyclization;
DOI:10.1021/ol006674w